For your complaints about the taskbar, yes I too find it incredibly annoying that they compress all the application windows into a tiny thumbnail but there is a setting to expand thumbnails to include titles and separate them if there are multiple windows which is what I use. I don't currently have access to my windows machine or I'd help you out with the exact setting but it's there somewhere in the "taskbar settings"
Yes there are limits to how long the title will go until it starts getting truncated so it is possible it won't fit a network path. I'm not sure if the behaviour of the taskbar was always to bring every window of an app to the foreground? But yes I don't think that's a thing either.
